201164-20-7

Usage

General Description

2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxylic acid is a chemical compound with the molecular formula C13H11F3O2. It consists of a cyclopropane ring attached to a carboxylic acid group and a phenyl group with a trifluoromethyl substituent. This chemical compound is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and bioactive molecules. Its unique structure and functional groups make it a versatile starting material for the production of complex organic compounds. Additionally, the trifluoromethyl group in 2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxylic acid can impart specific physiological properties to the molecules it is incorporated into, making it an important component in drug development and chemical synthesis.

Downstream Products

• 201164-22-9 (1S,2S)-2-(p-trifluoromethylphenyl)cyclopropylmethane 
• 201164-26-3 [(1S,2S)-2-(4-Trifluoromethyl-phenyl)-cyclopropyl]-methanol 

Relevant academic research and scientific papers

Substituted sulfonylaminoarylmethyl cyclopropanecarboxamide as VR1 receptor antagonists

This invention provides a compound of the formula (I): wherein A and B are independently CR12 or N; D and E are each independently CR9 or N; R1 represents (C1-C6)alkyl; R2 represents hydrogen, halogen, hydroxy, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy or (C1-C6)alkoxy-(C1-C6)alkyl; R3, R4, R5, R6, R10 and R11 each independently represent hydrogen, halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl or (C1-C6)alkoxy-(C1-C6)alkyl; or R3 and R4 are taken together with the carbon atom to which they are attached to form a 3- to 7-membered carbocyclic ring or heterocyclic ring in which one or two non-adjacent carbon atoms are optionally replaced by an oxygen atom, a sulfur atom or NH; R7 and R9 each independently represent hydrogen, halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, NH2, [(C1-C6)alkyl]NH—, [(C1-C6)alkyl]2N—, H2N—(C1-C6)alkoxy, (C1-C6)alkyl-NH—(C1-C6)alkoxy, [(C1-C6)alkyl]2N(C1-C6)alkoxy; H2N—(C1-C6)alkoxy-(C1-C6)alkyl, (C1C6)alkyl-NH—(C1-C6)alkoxy-(C1-C6)alkyl, [(C1-C6)alkyl]2N(C1-C6)alkoxy-(C1-C6)alkyl or 5- or 6-membered heterocyclic ring containing at least one nitrogen atom; R8 represents halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkoxy, halo(C1-C6)alkylsulfonyl, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkoxy, halo(C1-C6)alkylthio, [(C1-C6)alkyl]NH— or [(C1-C6)alkyl]2N—; or R7 and R8, when E is CR9, are taken together with the carbon atoms to which they are attached form a 5-8 membered carbocyclic or heterocyclic ring, in which one or two non-adjacent carbon atoms are optionally replaced by oxygen, sulfur, N or NH groups, wherein the carbocyclic ring or the heterocyclic ring is unsubstituted or substituted with one or more substituents each independently selected from the group consisting of hydroxy, (C1-C6)alkyl, (C1-C6)alkoxy and hydroxy(C1-C6)alkyl; and R12 represents hydrogen, halogen, (C1-C6)alkyl or hydroxy(C1-C6)alkyl; or a pharmaceutically acceptable salt or solvate thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of VR1 receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

A Substituted Hypersensitive Radical Probe for Enzyme-Catalyzed Hydroxylations: Synthesis of Racemic and Enantiomerically Enriched Forms and Application in a Cytochrome P450-Catalyzed Oxidation

The syntheses of racemic and enantiomerically enriched trans-1-methyl-2-(4-(trifluoromethyl)phenyl)cyclopropane (3) and the possible oxidation products from enzyme-catalyzed hydroxylation of 3 at the methyl group are reported. The important intermediate in the production of 3 was the Weinreb amide of the 2-arylcyclopropanecarboxylic acid which could be prepared in diastereomerically pure form and which also served as an intermediate for production of the cyclic oxidation products of 3. Hydroxylation of 3 by the cytochrome P450 isozyme CYP2B1 gave cyclic and ring-opened products. The product ratios support an insertion mechanism for the enzyme-catalyzed hydroxylation reaction in which minor amounts of rearranged products are produced by radical fragmentation within the transition structure of the insertion and by a competing reaction involving a cationic species. Formation of cationic rearrangement products by a heterolytic fragmentation reaction of a first-formed protonated alcohol product is suggested on the basis of the apparent amounts of cationic products formed in the hydroxylation of 3. This pathway for cation production appears to require that the activated enzyme complex (equivalent to enzyme-substrate-H2O2) oxidizes substrate before water dissociates to give an iron-oxo species.